N,N'-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazolium chloride

Description

N,N'-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazolium chloride is also known as1,3-Bis(2,6-Dibenzhydryl-4-Methoxyphenyl)-1H-Imidazol-3-Ium Chloride or IPr*OMe·HCl. It is a derivative of IPr*(1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazo-2-ylidene). IPr* and its derivatives have been shown to be helpful for the stabilization of catalytically active species.

Preparation

The synthesis begins with a solvent-free condensation of p-Anisidine and benzhydrol in the presence of HClconc. and ZnCl2. Then, the generated aniline was transformed into the diimine under acidic conditions using glyoxal and MgSO4 as a water abstractor. Subsequently, the cyclization towards the formation of the imidazolium salt was achieved with moderate yields by the use of p-formaldehyde under acidic conditions, assisted by the presence of ZnCl2 as a templating agent to obtain N,N'-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazolium chloride.